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The Humbling Tragedy of Jesse Jackson Jr.

Once considered a potential presidential candidate, the congressman and son of the famous civil-rights leader resigned his House seat as he negotiates with federal prosecutors. James Warren reports.

Congressman Jesse Jackson Jr. prides himself on being a student of the Civil War and has for years visited historic battlefields. So when he sent his letter of resignation (PDF) to House Speaker John Boehner on Wednesday, he might well have felt like the besieged Gen. Robert E. Lee surrendering at Appomattox Court House.

What once looked like to be a new era in both Chicago and national politics that began with his 1995 special-election victory to a South Side vacancy has crashed amid political, legal and physical disarray. A born-to-the-political-manor princeling has thrown up a white flag—and the worst may be yet to come.

Jackson has been under an ethical cloud since the election in 2008 of Barack Obama as the first black president—a distinction the namesake son of the famous civil-rights leader was once considered a frontrunner to achieve. The congressman aggressively pressed Gov. Rod Blagojevich to appoint him to the Senate seat that Obama had held, and a House investigation into his dealings with the now-jailed governor had been ongoing.

But Jackson’s departure was reportedly tied to his negotiating a plea agreement in an unrelated criminal investigation involving illegal use of campaign funds to renovate his house. In his letter of resignation—where he said he was stepping down “to focus on restoring my health—Jackson acknowledged that “I am aware of the ongoing federal investigation into my activities and I am doing my best to address the situation responsibly.”

Past the criminal probes, the 47-year-old Jackson’s marriage was challenged by reports of an extramarital affair with a bikini model and Washington waitress and, several months ago, he was hospitalized with bipolar disorder. He took a leave of absence from the House of Representatives in early June—though he did not publicly disclose that fact for more than two weeks and, successfully won reelection in his heavily Democratic district despite not campaigning for a single minute.

“It’s a terrible heart-rending tragedy,” said Mike Flannery, the dean of Chicago political reporters and mainstay of the local Fox affiliate. “He’s a guy who had the world just laid out for him and did little with the opportunity. And now he’s squandered the whole thing.”

The special election to fill Jackson’s seat is likely to be fiercely contested by local politicians. Will Burns, a Chicago alderman and former Obama legislative aide, is among those likely to run even as he conceded Wednesday that he wasn’t quite sure “what the political fallout will now be.”

“On a personal level, I have a lot of sympathy for him. I do think he offered something different and was a fresh face in the city,” said Burns.

Jackson did inspire a new generation of younger blacks to get involved in politics and built what could be seen as his own machine. He cultivated talent even as he tended to exhibit a distinct arrogance, a my-way-or-the-highway approach that rankled many in the city’s white political establishment including the powerful Daley family.

“In the end, he came to believe he was bulletproof; whether going after the Senate seat or the bikini model.”

Jackson himself took office in a 1995 special-election prompted by the resignation of Rep. Mel Reynolds, who left office after he was convicted of sexual assault and other charges from sleeping with a teenaged campaign volunteer. He ran for the seat against a field including a South Side state senator, Alice Palmer, whose decision to run prompted an unknown attorney, Barack Obama, to run for her state legislative seat. Another of the candidates Jackson defeated in that race, Emil Jones, would become an important mentor to neophyte State Sen. Obama, who wound up in Springfield with scant public notice while Jackson headed to the nation’s capital amid significant fanfare.

He was, after all, the son and namesake of Jesse Jackson, the civil-rights leader and 1988 candidate for the Democratic presidential nomination. Jackson Jr.’s victory was seen as heralding an progressive new era in Chicago’s South Side politics, as he had bested an ethically muddy political machine.

Flannery recalled having breakfast with Jackson, his wife Sandi, and his mother at the mother’s Washington home on the morning that Jackson was sworn in by House Speaker Newt Gingrich. They were ebullient, he remembered, and at one point the new congressman took the reporter aside and sought his counsel.

The journalist, who was raised in the capital, warned him that too many Washington politicians “start believing their own baloney” and get big heads. “’Don’t believe your own baloney,’” he recalled telling young Jackson, who would subsequently quote that admonition at his own press conferences.

For sure, he could point to many accomplishments, as he did in his letter to Boehner:

“Along this journey we have accomplished much,” he said. “We have built new train stations, water towers, and emergency rooms. We have brought affordable housing, community centers and healthcare clinics to those that need it most. In all, nearly a billion dollars of infrastructure and community improvement has been made on the South Side of Chicago and thousands of new jobs have been created.”

Better times: Watch Jesse Jackon Jr.'s March 2012 victory speech.

But there is the sense in Chicago that he did begin to believe his own baloney, and many saw him as squandering the cachet he possessed as Rev. Jackson’s offspring and a congressman while in his early 30s.Even his place on the House Appropriations Committee—one of the most influential and sought-after panels, because of its control over how government money is spent—was not exploited in the ways it might have been, according to Illinois delegation members who have long found him something of a poseur and a disappointment.

“He was born on third base and thought he had hit a triple,” Flannery said. “And, in the end, he came to believe he was bulletproof; whether going after the Senate seat or the bikini model. He came to think of himself as invulnerable.”

His Blagojevich troubles involved the nexus of his personal ambition and the governor’s belief that the Senate seat Obama had left was “fucking golden.” A Jackson fundraiser told government prosecutors that Jackson had urged him to offer Blagojevich millions of dollars in return for picking Jackson for the Obama Senate vacancy—a claim that Jackson, while acknowledging his interest in the position, denied. While Blagojevich was eventually convicted for his attempts to peddle the seat, Jackson was never indicted but the House had continued to probe his conduct, an investigation that ends with his resignation.

The famous father of the congressman has been deeply supportive in recent months, though their relationship has long been frayed, in part because of the father’s ever-roaming ways, and the son’s closeness to his mother, Jacqueline Jackson.

The son is a more polished, if less genuine, character than the whirling-dervish, passionate, and even bombastic icon of a father. He was educated at an elite Washington prep school and has been seen as more disciplined. He’s a good public speaker, if not given to the rhetorical flights of the father, and was a superior student of political mechanics and tactics.

'I’m not ashamed to say he thought he was going to be a senator. He thought he was going to have a chance to run for mayor,” Jacqueline Jackson, the congressman’s mother, told supporters earlier this year. And politically it was indeed once distinctly possible to see him as mayor—or even America’s first black president. He did in fact construct a South Side political apparatus that was far more effective than those of the city’s other, woefully underperforming longtime lackeys, congressmen Bobby Rush and Danny Davis. At least until the Blagojevich mess, Jackson was a force to be reckoned with in the city and at times in Congress.

He’d confronted and long been considered a likely successor to the 22-year reign of Mayor Richard M. Daley, son of the legendary big city boss Richard J. Daley. But when Daley announced he was retiring two years ago, a combination of Jackson’s suspect ties to the Blagojevich debacle, along with a powerful rival in then-candidate and now mayor Rahm Emanuel, helped clear him from the field.

In the end, Jesse Jackson Jr.’s story is a tragic one. Eclipsed for most of his life by his father, he was then marginalized by Obama. And now he has been brought to his knees by self-inflicted wounds. The history buff is surely aware that he is unlikely to be allowed to ride off as quietly as General Lee.